2-Chlorobenzothiazole → HCID 178429377, compound

Participants

Reaction Steps

A solution of 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride, INTERMEDIATE 62, (0.100 g, 0.372 mmol), 2-chlorobenzothiazole (0.095 mL, 0.558 mmol), and N,N-diisopropylethylamine (0.194 mL, 1.116 mmol) in DMSO (0.4 mL) was stirred at 120° C. for 4 h. The reaction was allowed to cool to room temperature, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silica gel column eluting with 0-60% EtOAc/hexane to give the title compound 7-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.082 g, 0.224 mmol, 60.3% yield) as brown solid. m/z: 366.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.84 (s, 1 H), 8.33 (s, 1 H), 7.60 (dd, J=13.11, 7.82 Hz, 2 H), 7.23-7.39 (m, 1 H), 6.99-7.18 (m, 1 H), 6.26 (br. s., 1 H), 5.15-5.40 (m, 1 H), 4.53-4.70 (m, 1 H), 3.33-3.55 (m, 2 H), 2.41-2.58 (m, 2 H), 1.36-1.55 (m, 6 H).

Provenance & Evidence